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. 2020 Sep 29;48(18):10101–10124. doi: 10.1093/nar/gkaa750

Scheme 2.

Scheme 2.

Reagents and conditions: (i) 80% aq. TFA/DCM, 0°C to room temperature, overnight; 83% for 5, 70% for 15. (ii) Benzoic anhydride, DMAP/pyridine, room temperature, overnight; 99% for 6 and for 16. (iii) TBAF/THF, room temperature, overnight; 87% for 7, 94% for 17. (iv) DMTrCl, AgNO3/THF/pyridine (THF/pyridine, 4:1, v/v), room temperature, overnight; 98% for 8, 98% for 18. (v) NaOH/THF/MeOH (THF/MeOH, 1:1, v/v), 0°C, 30 min; 96% for 9 and for 19. (vi) TBSCl, AgNO3/THF/pyridine (THF/pyridine, 4:1, v/v), room temperature, overnight; 50% for 10, 53% for 20. (vii) i-Pr2NP(Cl)O(CH2)2CN, DIPEA, 1-methylimidazole/DCM, room temperature, 2 h; 88% for 11, 65% for 21. (viii) 1) Succinic anhydride, DMAP/DCM, room temperature, overnight. 2) LCAA-CPG (pore size 500 Å, 171 μmol/g), HBTU, DIPEA/DMF, room temperature, overnight. 3) Acetic anhydride/pyridine, room temperature, overnight; 70 μmol/g loading for 12, 97 μmol/g for 22.